Wearing a T-Shirt With Dress Shoes: How to Pull It Off

It’s always a little challenging style-wise to pair a traditionally casual piece with a dressier one and do so without looking like you’re mismatched and don’t know what you’re doing. T-shirts and lace-up shoes definitely exist on opposite ends of the style and formality spectrum but there’s a right way to wear them both without sending out mixed signals. It may even end up being your favorite way to both style-up your favorite tee and dress-down a pair of dressier bottoms. Here’s how.

Don’t reach for anything graphic

Man wearing a basic T-shirt | Pablo Cuadra/Getty Images

As a general rule, when you’re pairing a casual piece such as a T-shirt with dress shoes, you want to steer clear of shirts with graphics or noticeable large logos. Although vintage tees with cool Harley graphics are great “do” when you’re wearing appropriate matching boots or a pair of sneakers — it looks like have don’t have a clue what you’re doing if you’re pairing it with dressy lace-up shoes. A dressier shoe calls for a dressier-looking T-shirt. Opt for solids and stripes, which still look easy-going without drawing too much attention to your chest.

Yes to chinos

Man wearing chinos | Mrporter.com

In order to get this T-shirt pairing with dress shoes right, you may have to leave your jeans out of it and give them the day off. Chinos are inherently more clean-cut than denim, and if you get the right, tailored pair you can absolutely pull off the T-shirt/dress shoes combo perfectly.

Coordination is key

Coordinating colors always works well | Pablo Cuadra/Getty Images

When it comes to coordinating the color of your outfits, this rule rings especially true when you’re pairing together style opposites like casual and dressy. Keep the anchors of your outfit in harmony: If your T-shirt is black, then reach for a pair of black shoes. The same or similar goes if you opt for a olive green tee, which calls for brown shoes in the same color spectrum. Be careful though if you’re looking to wear a blue or a red tee, which can go either way, in which case, defer to your pants.

Accessorize with man jewelry

Man’s accessories | iStock.com

To complete the look and drive home the idea that you didn’t accidentally leave your suit jacket at home (especially if someone takes a look down at your shoes), throw on a necklace or a metal bracelet. Not only will it add some necessary intrigue to your look, but it will serve as an stand-in for a necktie in some alternate universe.